engineering degree never taught them how to look at historical social context or put themselves into the shoes of someone not like them

Honestly I went to an almost pure engineering school and it's really not that hard. In fact I literally had one of my few humanities classes where I wrote an essay about people who believe in conspiracies and aliens from a psychological perspective (it wasn't that deep, or technical though).

IDK. I think really what it takes is someone, anyone challenging you to think about things from all sides. Don't just accept what someone says at face value if it doesn't make sense. Ask questions. Be skeptical.